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. 2019 May 28;10:571. doi: 10.3389/fphar.2019.00571

TABLE 1.

Characterization of in vivo metabolites of Datura metel seeds by UPLC/ESI/qTOF-MS and Q-Trap LC/MS/MS in this study.

No. RT
 Formula HR-MS [M+H]+
 (+)ESI-MSn(m/z) Metabolic Reaction Plasma Urine Feces
(min) Measured Predicted Δ (ppm) Source
*1 4.32 C14H14N2O3 259.1072 259.1077 1.9 MS2[259]: 240,162,150,114 Daturametelindole B – – + DS,DW
a 1-M1 3.17 C20H22N2O9 453.1405 453.1398 –1.5 MS2[453]: 340,150 +GluA + ++ ++ DS,DW
MS3[150]: 114
1-M2 3.68 C14H14N2O6S 339.0652 339.0645 –2.1 MS2[339]: 321,150 +Sul ++ + – DS,DW
MS3[150]: 122,114
1-M3 5.28 C14H12N2O3 257.0913 257.0921 3.1 MS2[257]: 150,136,122 −2H – + – DS
2 4.48 C28H36O4 437.2689 437.2686 –0.7 MS2[437]: 283,258,240,150 Paraminabeolide A + + – DW
*3 4.52 C28H42O6 475.3022 475.3054 6.7 MS2[475]: 305,135,170 Daturametelins M + + – DS,DW
3-M1 4.03 C28H40O5 457.2956 457.2949 –1.5 MS2[457]: 287,163,149 -H2O + + ++ DS,DW
3-M2 4.24 C28H44O8 509.3112 509.3109 –0.6 MS2[509]: 340,136 +H2O+OH + + ++ DS,DW
3-M3 4.36 C28H42O7 491.3001 491.3003 –0.4 MS2[491]: 323,155,135 +OH + + – DS,DW
3-M4 4.42 C29H44O6 489.3229 489.3212 –3.4 MS2[489]: 319,136 +CH3 – + + DS
4 4.54 C34H48O11 633.3274 633.3269 –0.8 MS2[633]: 469,453,203,150 Baimantuoluoside C + – – DW
4-M1 3.69 C33H46O14S 699.2673 699.2681 1.1 MS2[699]: 619,455 +Sul-CH3 + + – DW
MS3[455]: 273,187,163,136
4-M2 4.18 C34H46O11 631.3119 631.3113 –1.0 MS2[631]: 467,288,136 −2H – ++ – DW
4-M3 4.35 C40H56O17 809.3598 809.3590 –0.9 MS2[809]: 633,469,295,136 +GluA – ++ – DW
*5 4.60 C28H40O6 473.2887 473.2898 2.3 MS2[473]: 301,206,171 Hyoscyamilactol + + ++ DS,DW
5-M1 4.13 C28H40O7 489.2838 489.2847 1.8 MS2[489]: 338,317,171,135 +OH ++ + + DS,DW
6 5.38 C30H39ClO8 563.2412 563.2406 –1.0 MS2[563]: 409,393,260,153 Physagulin I + + + DW
6-M1 4.31 C30H39ClO11S 643.1985 643.1974 –1.7 MS2[643]: 563,409,164 +Sul – + + DW
6-M2 4.95 C36H45ClO14 737.2583 737.2571 –1.6 MS2[737]: 561,407,150 +GluA-2H – – + DW
7 5.86 C30H42O9 547.2879 547.2902 4.2 MS2[547]: 393,240,153,114 Physagulin K – + + DW
8 5.92 C34H50O12 651.3371 651.3375 0.6 MS2[651]: 487,319,288,163 Coagulin L + + – DW
*9 6.12 C14H14N2O2 243.1116 243.1128 4.9 MS2[243]: 215,187,107 Daturametelindole A + + + DS,DW
a 9-M1 2.75 C20H20N2O8 417.1297 417.1292 –1.2 MS2[417]: 241,150,134 +GluA-2H – – ++ DS,DW
a 9-M2 4.69 C20H22N2O9 435.1388 435.1398 2.3 MS2[435]: 259,231,136 +GluA+OH ++ + – DS,DW
9-M3 5.28 C15H16N2O2 257.1296 257.1285 –4.2 MS2[257]: 243,215,136,107 +CH3 + + ++ DS,DW
a 9-M4 5.82 C20H22N2O11S 499.1002 499.1017 3.0 MS2[499]: 419,243,150 +GluA+Sul + + – DS,DW
9-M5 6.49 C13H12N2O5S 309.0532 309.0540 2.5 MS2[309]: 229,136,122 +Sul-CH3 ++ + – DS,DW
9-M6 6.68 C14H14N2O6S 339.0652 339.0645 –2.0 MS2[339]: 259,243,215 +Sul+OH ++ ++ – DS,DW
*10 7.52 C34H48O11 633.3244 633.3269 3.9 MS2[633]: 469,437 Dinoxin B + ++ + Ds, Dw
MS3[469]: 285,136
10-M1 5.88 C34H48O12 649.3251 649.3219 –4.9 MS2[649]: 483,299,136 +OH + ++ + DS,DW
10-M2 6.03 C35H50O11 647.3442 647.3426 –2.4 MS2[647]: 483,471,285 +CH3 + + ++ DS,DW
a 10-M3 7.06 C40H56O17 809.3586 809.3590 0.5 MS2[809]: 437,469,246,136 +GluA + ++ ++ DS,DW
10-M4 8.44 C34H46O11 631.3132 631.3113 –3.0 MS2[632]: 467,421,228,114 -2H + + + DS,DW
10-M5 9.78 C28H35O6 468.2533 468.2506 –5.7 MS2[468]: 283,134 -Glc-2H – + + DS,DW
11 8.14 C28H38O5 455.2799 455.2792 –1.5 MS2[455]: 287,167,152,135 Withawrightolide – – + DW
12 8.36 C38H54O15 751.3517 751.3535 2.3 MS2[751]: 589,419,331,193 Chantriolide C – – + DW
12-M1 8.51 C44H62O21 927.3855 927.3856 0.1 MS2[927]: 751,589,419 +GluA – – ++ Dw
MS3[419]: 331,193,155,134
12-M2 7.58 C37H52O18S 817.2951 817.2947 –0.5 MS2[817]: 737,575,405,193 +Sul-CH3 – – + DW
12-M3 7.62 C38H56O17 785.3573 785.3590 2.1 MS2[785]: 391,357,193,163 +OH+H2O – – ++ DW
12-M4 8.00 C39H56O16 781.3628 781.3641 1.6 MS2[781]: 391,373,355,193,163 +OH+CH3 – – ++ DW
12-M5 14.98 C38H52O15 749.3361 749.3379 2.4 MS2[749]: 357,283,193,163 -2H – – ++ DW
*13 8.73 C28H36O5 453.2654 453.2636 –3.9 MS2[453]: 341,285,167,114 Withametelin L ++ ++ ++ DS,DW
13-M1 7.74 C27H34O8S 519.2055 519.2047 –1.5 MS2[519]: 439,271,167,150 +Sul-CH3 + + + DS,DW
13-M2 8.19 C28H36O6 469.2574 469.2585 2.3 MS2[469]: 301,269,167 +OH ++ ++ ++ DS,DW
14 8.91 C34H52O10 621.3642 621.3633 –1.4 MS2[621]: 509,457 Coagulin Q + + + Dw
MS3[457]: 314,287,163,135
15 9.05 C29H42O8 519.2957 519.2950 –1.3 MS2[519]: 319,295,262,199,165 Baimantuoluoline C + + + DW
15-M1 7.56 C29H42O9 535.2914 535.2902 –2.2 MS2[535]: 509,335,199,165 +OH ++ + + DW
16 9.40 C28H40O7 489.2856 489.2847 –1.8 MS2[489]:439,317,353,171 Philadelphicalactone A – + + DW
17 9.43 C33H48O11 621.3288 621.3269 –3.0 MS2[621]: 457,289,136 Withalongolide L + ++ – DW
17-M1 7.37 C33H48O14S 701.2834 701.2838 –0.5 MS2[701]: 621,457,289,136 +Sul – ++ ++ DW
*18 9.77 C14H14N2O5 291.0968 291.0975 2.4 MS2[291]: 246,219,155,135 Daturametelindole D + + ++ DS,DW
18-M1 7.48 C13H12N2O8S 357.0391 357.0387 –1.1 MS2[357]: 277,144,135 +Sul-CH3 + + ++ DS
18-M2 8.43 C14H14N2O8S 371.0538 371.0544 1.6 MS2[371]: 291,155,135 +Sul – + ++ DS,DW
*19 10.86 C18H19NO4 314.1366 314.1387 6.6 MS2[314]: 314,177,163 N-trans-feruloyltyramine – – ++ DW
a 19-M1 8.50 C24H27NO11 506.1669 506.1657 –2.3 MS2[506]: 330,314,177,145 +GluA+OH ++ + – DW
19-M2 8.14 C18H19NO5 330.1339 330.1336 –0.9 MS2[330]: 177,137 +OH ++ + – DW
19-M3 9.65 C18H17NO4 312.1232 312.1230 –0.6 MS2[312]: 177,145,114 -2H ++ ++ ++ DW
*20 10.91 C15H18O2 231.1377 231.1380 1.3 MS2[231]: 215,203,190,136 Cinerolide + + ++ DS,DW
a 20-M1 6.46 C21H24O8 405.1552 405.1544 –1.9 MS2[405]: 229,187,201,134 +GluA-2H + + – DS,DW
20-M2 8.60 C15H18O5S 311.0934 311.0948 4.5 MS2[311]: 231,190,136 +Sul ++ + – DS,DW
20-M3 9.92 C14H16O2 217.1211 217.1223 5.5 MS2[217]: 189,174 -CH3 + + – DS
21 12.10 C40H62O15 783.4153 783.4161 1.0 MS2[783]: 457,355,325,288 Withanoside IV – + – DW
21-M1 8.06 C41H64O16 813.4274 813.4267 –0.8 MS2[814]: 487,325,318,226,288 +OH+CH3 – ++ ++ DW
*22 12.87 C18H22N2O4 331.1660 331.1652 –2.4 MS2[331]: 325,223,189,107 Daturametelindole C ++ + – DS,DW
22-M1 8.21 C17H20N2O7S 397.1068 397.1064 –1.0 MS2[397]: 317,209,107 +Sul-CH3 ++ ++ ++ DS,DW
22-M2 10.07 C17H20N2O4 317.1487 317.1496 2.8 MS2[317]: 209,150,107 -CH3 ++ + – DS,DW
23 12.93 C28H40O5 457.2945 457.2949 0.8 MS2[457]: 285,171,151,147 Cilistol A – – + DW
23-M1 8.96 C34H48O11 633.3257 633.3269 1.9 MS2[633]: 457,171,151 +GluA – – + DW
24 13.09 C40H62O15 783.4154 783.4161 0.9 MS2[783]: 457,325,289,162 Withanoside VI – – + DW
25 13.21 C28H38O9 519.2577 519.2589 2.3 MS2[520]: 349,197,137 Withangulatin B – – + DW
26 13.41 C30H42O7 515.3018 515.3003 –2.9 MS2[515]: 343,329,193,171,150 Virginol C – + + DW
26-M1 15.29 C36H50O14 707.3282 707.3273 –1.2 MS2[708]: 532,359,193,171,166 +GluA+OH – ++ ++ DW
27 13.48 C28H40O8 505.2786 505.2796 1.9 MS2[505]: 319,264,185,136 Ajugin D + – – DW
27-M1 10.24 C34H48O17S 761.2674 761.2685 1.4 MS2[761]: 585,505,319,185 +GluA+Sul – – ++ DW
28 13.98 C28H40O9 521.2747 521.2745 –0.4 MS2[521]: 351,255,184,169 Phyperunolide E – – + DW
28-M1 4.63 C34H48O15 697.3059 697.3066 1.0 MS2[697]: 521, 351,203,169 +GluA – + – DW
28-M2 14.5 C27H38O9 507.2578 507.2589 2.1 MS2[508]: 351,184,167,155 -CH3 – + – DW
*29 14.11 C35H50O10 631.3441 631.3477 5.7 MS2[631]: 566,467 Daturametelin L – + + Ds, Dw
MS3[467]: 299,162,136
29-M1 9.60 C35H50O11 647.3439 647.3426 –2.0 MS2[647]: 483,469,285,135 +OH + + – DS,DW
a 29-M2 10.61 C41H58O16 807.3781 807.3798 2.1 MS2[807]: 631,453,285,135 +GluA – ++ ++ DS,DW
*29-M3 14.93 C34H48O10 617.3315 617.3320 0.8 MS2[617]: 453,441,285,135 -CH3 (30) – ++ + DW
29-M4 15.15 C29H37O5 466.2720 466.2714 –1.2 MS2[466]: 453,285,134 -Glc-2H – ++ ++ DW
*30 14.93 C34H48O10 617.3312 617.3320 1.3 MS2[617]: 453, 285,271,135 Daturametelin I – ++ + DW
a 30-M1 4.53 C34H48O11 633.3242 633.3269 4.2 MS2[633]: 469,285,136 +OH – + + DW
*31 15.08 C36H36N2O8 625.2521 625.2544 3.6 MS2[625]:488,377,298,164,136 Cannabisin F – + ++ DW
a 31-M1 8.83 C42H44N2O15 817.2854 817.2814 –4.8 MS2[817]:641,611,488,373,298 +GluA+OH – + ++ DW
31-M2 9.28 C35H34N2O8 611.2368 611.2388 3.2 611,474,373,298,136 -CH3 + + ++ DW
*32 15.21 C30H48O2 441.3712 441.3727 3.3 MS2[441]: 423,357,150 Daturaolone – – ++ DS,DW
a 32-M1 7.54 C36H56O9 633.3999 633.3997 –0.3 MS2[633]: 457,435,114 +GluA+OH + – – DS
33 15.35 C33H48O10 605.3317 605.3320 0.4 MS2[605]: 441,273,148,138 Withalongolide M – – + DW
33-M1 7.10 C33H48O14S 701.2854 701.2838 –2.2 MS2[701]: 621,457,289,135 +Sul+OH ++ + – DW
34 15.39 C28H42O9S 555.2606 555.2622 2.8 MS2[555]: 357,299,150 Cilistol Y + + + DW
35 15.53 C34H56O11 641.3874 641.3895 3.2 MS2[642]: 429,385,341,150 Cilistol J – – + DW
*36 15.62 C34H48O10 617.3315 617.3320 0.8 MS2[617]: 453,285,136 Daturataturin A – + + DW
*36-M1 7.53 C34H48O11 633.3247 633.3269 3.4 MS2[633]: 469,285,136 +OH (10) ++ + + DW
a 36-M2 7.82 C40H54O16 791.3451 791.3485 4.2 MS2[791]: 617,451,268,133 +GluA-2H + – – DW
36-M3 9.52 C35H50O10 631.3496 631.3477 –3.0 MS2[631]: 453,299,136 +CH3 + + – DW
36-M4 11.63 C28H36O5 453.2653 453.2636 –3.7 MS2[454]: 437,283,136 -Glc-2H + ++ ++ DW
37 16.68 C28H36O6 469.2565 469.2585 4.2 MS2[469]: 316,270,153,136,122 Exodeconolide A + + + DW
38 17.03 C34H52O11 637.3568 637.3582 2.1 MS2[637]: 457,285,185,153 Withanoside XI – ++ ++ DW
38-M1 8.03 C40H60O17 813.3912 813.3903 –1.1 MS2[813]: 637,457,285,185 +GluA ++ ++ ++ DW
39 17.58 C28H36O7 485.2521 485.2534 2.6 MS2[485]: 315,176,169,151 20-Hydroxytubocapsanolide A – – + DW
*40 17.74 C17H17NO3 284.1286 284.1281 –1.7 MS2[284]: 147,136,122 n-trans-p-coumaroyltyramine ++ ++ ++ DS,DW
40-M1 10.96 C17H19NO5 318.1358 318.1336 –6.9 MS2[318]: 274,230,150,114 +OH+H2O ++ ++ ++ DS,DW
40-M2 12.93 C17H17NO4 300.1211 300.1230 6.3 MS2[300]: 152,114 +OH ++ + + DS,DW
a 40-M3 13.24 C23H25NO9 460.1623 460.1602 –4.5 MS2[460]:284,136 +GluA + ++ ++ DS,DW
40-M4 14.09 C17H17NO6S 364.0833 364.0849 4.3 MS2[364]:284,147,136 +Sul + ++ ++ DS,DW
40-M5 16.33 C23H23NO9 458.1437 458.1446 1.9 MS2[458]: 282,147,134 +GluA-2H – + ++ DS,DW
*41 18.08 C29H48O 413.3790 413.3778 –2.9 MS2[413]: 273,139,135 Stigmasterol ++ ++ – DS,DW
41-M1 8.74 C29H48O2 429.3741 429.3727 –3.2 MS2[429]: 289,274,139 +OH ++ + – DS,DW
41-M2 12.08 C29H46O3 443.3509 443.3520 2.4 MS2[443]: 289,196,153,141,135 +2OH + + – DS,DW
41-M3 13.42 C29H50O3S 479.3563 479.3553 –2.0 MS2[479]: 399,275,137 +2H+Sul – + ++ DS,DW
42 18.43 C28H40O7 489.2821 489.2847 5.3 MS2[489]: 319,169,151 Jaborosalactone VIII + – – DW

*,Identified by comparing with reference standards; ++, detected at high abundance, > 1 × e4; +, only detected, 1 × e3 ∼ 1 × e4; –, not detected. a Confirmed by enzyme hydrolysis. DS, detected in single compound administration biosamples; DW, detected in WDS administration biosamples.